WO1994022986A1 - Poly(vinyl ether) aminocarbamates and fuel compositions containing the same - Google Patents
Poly(vinyl ether) aminocarbamates and fuel compositions containing the same Download PDFInfo
- Publication number
- WO1994022986A1 WO1994022986A1 PCT/US1994/003302 US9403302W WO9422986A1 WO 1994022986 A1 WO1994022986 A1 WO 1994022986A1 US 9403302 W US9403302 W US 9403302W WO 9422986 A1 WO9422986 A1 WO 9422986A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- carbon atoms
- fuel
- alkyl
- vinyl ether
- poly
- Prior art date
Links
- 239000000446 fuel Substances 0.000 title claims description 51
- 239000000203 mixture Substances 0.000 title claims description 40
- -1 Poly(vinyl ether) Polymers 0.000 title abstract description 218
- OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical class NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 title abstract description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 103
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 61
- 229920000768 polyamine Polymers 0.000 claims abstract description 51
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 23
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 18
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 15
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 15
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 15
- 238000009835 boiling Methods 0.000 claims abstract description 13
- 239000003502 gasoline Substances 0.000 claims abstract description 13
- 239000002283 diesel fuel Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 20
- 239000012141 concentrate Substances 0.000 claims description 16
- 229920001281 polyalkylene Polymers 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 11
- 239000005977 Ethylene Substances 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 239000012530 fluid Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000003599 detergent Substances 0.000 claims description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 238000002485 combustion reaction Methods 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 2
- IVHKZGYFKJRXBD-UHFFFAOYSA-N amino carbamate Chemical compound NOC(N)=O IVHKZGYFKJRXBD-UHFFFAOYSA-N 0.000 abstract description 16
- 239000002816 fuel additive Substances 0.000 abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 230000002265 prevention Effects 0.000 abstract description 2
- 239000000178 monomer Substances 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 33
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 229920000642 polymer Polymers 0.000 description 21
- 239000000654 additive Substances 0.000 description 18
- 150000001412 amines Chemical group 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000010550 living polymerization reaction Methods 0.000 description 14
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 14
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000012442 inert solvent Substances 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 150000001298 alcohols Chemical class 0.000 description 11
- 150000001336 alkenes Chemical class 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 238000012360 testing method Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 7
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 238000005804 alkylation reaction Methods 0.000 description 6
- 230000000977 initiatory effect Effects 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- 239000004711 α-olefin Substances 0.000 description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 238000010791 quenching Methods 0.000 description 4
- 230000000171 quenching effect Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- REEBWSYYNPPSKV-UHFFFAOYSA-N 3-[(4-formylphenoxy)methyl]thiophene-2-carbonitrile Chemical compound C1=CC(C=O)=CC=C1OCC1=C(C#N)SC=C1 REEBWSYYNPPSKV-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
- 229920001083 polybutene Polymers 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- GYTOJALPPLZKKP-UHFFFAOYSA-N 1-(2-chloroethoxy)prop-1-ene Chemical compound CC=COCCCl GYTOJALPPLZKKP-UHFFFAOYSA-N 0.000 description 1
- JNMJJTLOYAEWAV-UHFFFAOYSA-N 1-bromo-3-ethenoxypropane Chemical compound BrCCCOC=C JNMJJTLOYAEWAV-UHFFFAOYSA-N 0.000 description 1
- PNEWSCXZLUPKET-UHFFFAOYSA-N 1-chloro-4-ethenoxybutane Chemical compound ClCCCCOC=C PNEWSCXZLUPKET-UHFFFAOYSA-N 0.000 description 1
- NYRMKWYDURACJJ-UHFFFAOYSA-N 1-dodecyl-4-(2-ethenoxyethoxy)benzene Chemical compound CCCCCCCCCCCCC1=CC=C(OCCOC=C)C=C1 NYRMKWYDURACJJ-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical group NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 description 1
- FDIPWBUDOCPIMH-UHFFFAOYSA-N 2-decylphenol Chemical compound CCCCCCCCCCC1=CC=CC=C1O FDIPWBUDOCPIMH-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- GNUGVECARVKIPH-UHFFFAOYSA-N 2-ethenoxypropane Chemical compound CC(C)OC=C GNUGVECARVKIPH-UHFFFAOYSA-N 0.000 description 1
- ZQWSENBIABALKM-UHFFFAOYSA-N 2-hexacosylphenol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCC1=CC=CC=C1O ZQWSENBIABALKM-UHFFFAOYSA-N 0.000 description 1
- HMWIHOZPGQRZLR-UHFFFAOYSA-N 2-hexadecylphenol Chemical compound CCCCCCCCCCCCCCCCC1=CC=CC=C1O HMWIHOZPGQRZLR-UHFFFAOYSA-N 0.000 description 1
- QEMHBAGGYKJNSS-UHFFFAOYSA-N 2-icosylphenol Chemical compound CCCCCCCCCCCCCCCCCCCCC1=CC=CC=C1O QEMHBAGGYKJNSS-UHFFFAOYSA-N 0.000 description 1
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 description 1
- WCRKLZYTQVZTMM-UHFFFAOYSA-N 2-octadecylphenol Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=CC=C1O WCRKLZYTQVZTMM-UHFFFAOYSA-N 0.000 description 1
- RGDDVTHQUAQTIE-UHFFFAOYSA-N 2-pentadecylphenol Chemical compound CCCCCCCCCCCCCCCC1=CC=CC=C1O RGDDVTHQUAQTIE-UHFFFAOYSA-N 0.000 description 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
- WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 1
- JOONSONEBWTBLT-UHFFFAOYSA-N 2-tetradecylphenol Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1O JOONSONEBWTBLT-UHFFFAOYSA-N 0.000 description 1
- OREKREJVUNVFJP-UHFFFAOYSA-N 2-triacontylphenol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1=CC=CC=C1O OREKREJVUNVFJP-UHFFFAOYSA-N 0.000 description 1
- UVNKQUXHHOZJLS-UHFFFAOYSA-N 2-undecylphenol Chemical compound CCCCCCCCCCCC1=CC=CC=C1O UVNKQUXHHOZJLS-UHFFFAOYSA-N 0.000 description 1
- NNPLPIIEFPCNST-UHFFFAOYSA-N 4-(2-ethenoxyethyl)isoindole-1,3-dione Chemical compound C=COCCC1=CC=CC2=C1C(=O)NC2=O NNPLPIIEFPCNST-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- KJWMCPYEODZESQ-UHFFFAOYSA-N 4-Dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C=C1 KJWMCPYEODZESQ-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- ANHQLUBMNSSPBV-UHFFFAOYSA-N 4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical group C1=CN=C2NC(=O)COC2=C1 ANHQLUBMNSSPBV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000007854 aminals Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000006079 antiknock agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- KFDKSWDECHPONU-UHFFFAOYSA-N bis(trichloromethyl) carbonate Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl.ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl KFDKSWDECHPONU-UHFFFAOYSA-N 0.000 description 1
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- SZMNDOUFZGODBR-UHFFFAOYSA-N decan-5-ol Chemical compound CCCCCC(O)CCCC SZMNDOUFZGODBR-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical compound NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- UVRNDTOXBNEQBA-UHFFFAOYSA-N trichloromethyl carbonochloridate Chemical compound ClC(=O)OC(Cl)(Cl)Cl.ClC(=O)OC(Cl)(Cl)Cl UVRNDTOXBNEQBA-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/16—Hydrocarbons
- C10L1/1608—Well defined compounds, e.g. hexane, benzene
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/16—Hydrocarbons
- C10L1/1616—Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/16—Hydrocarbons
- C10L1/1625—Hydrocarbons macromolecular compounds
- C10L1/1633—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds
- C10L1/1641—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds from compounds containing aliphatic monomers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
- C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
- C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
- C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
- C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
- C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C)
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/30—Organic compounds compounds not mentioned before (complexes)
- C10L1/305—Organic compounds compounds not mentioned before (complexes) organo-metallic compounds (containing a metal to carbon bond)
Definitions
- This invention relates to novel end-functionalized poly(vinyl ethers) . More particularly, this invention relates to novel poly(vinyl ether) aminocarbamates and their use in fuel compositions to prevent and control engine deposits.
- Deposit control additives differ in their effectiveness for preventing or controlling deposits on various engine components. This is believed to be due primarily to the fact that each engine component has a different operating temperature and some deposit control additives are not sufficiently stable on the surface of certain engine components to perform their intended function. In this regard, deposits on intake valves are particularly difficult to control, since intake valve operating temperatures can exceed 300 ⁇ C. At such high temperatures, many fuel additives are too volatile to be effective, while others thermally decompose.
- the present invention discloses a new class of poly(vinyl ether) aminocarbamate fuel additives having such properties.
- Polyether fuel additives are well known in the art. These polyether additives, however, have a poly(oxyalkylene) "backbone", i.e. the polyether portion of the molecule consists of repeating oxyalkylene units, i.e. [-CHR-CHR-0-] x . In contrast, the fuel additives of the present invention have a vinyl ether polymer backbone consisting of repeating vinyl ether units, i.e. [-CHR-CR(OR)-] ⁇ .
- U.S. Patent No. 4,191,537, issued March 4, 1980 to R. A. Lewis et al. discloses a fuel composition comprising a major portion of hydrocarbons boiling in the gasoline range and from 30 to 2000 ppm of a hydrocarbyl poly(oxyalkylene) aminocarbamate having a molecular weight from about 600 to 10,000, and at least one basic nitrogen atom.
- the hydrocarbyl poly(oxyalkylene) moiety is composed of oxyalkylene units selected from 2 to 5 carbon oxyalkylene units.
- End-functionalized poly(vinyl ethers) are also known in the art.
- A. Verma et al. in Polymer Preprints, 1991, 32 , 322 describe the synthesis and characterization of functionalized poly(butyl vinyl ether) oligomers having an aldehyde or a primary hydroxyl endgroup.
- These poly(vinyl ethers) are prepared by the living polymerization of butyl vinyl ether using a hydrogen iodide/zinc iodide initiating system. The polymerization reaction is terminated with aqueous potassium carbonate to form the aldehyde endgroup, which can subsequently be reduced to form the primary hydroxyl endgroup.
- Poly(vinyl ethers) having amine end-groups are also known.
- C. G. Cho et al.. Polymer Preprints , 1987, 28 , 356, describe the synthesis of amine-terminated poly(alkyl vinyl ethers) by quenching the living polymerization of alkyl vinyl ethers with p-methyl styrene and an amine.
- the resulting poly(alkyl vinyl ether) is covalently linked to the amine through a p-methyl styrenic unit.
- Amine-terminated poly(isobutyl vinyl ethers) having a primary amine at the beginning of the vinyl ether polymer are described by T. Hashimoto et al. in J. Poly. Sci . Polym . Chem . Ed . , 1990, 28 , 1137. These poly(vinyl ethers) are prepared by initiating the living polymerization of isobutyl vinyl ether with 2-(vinyloxy)ethyl phthalimide. The phthalimide group is then removed with hydrazine to produce a poly(isobutyl vinyl ether) having a 2-aminoethyl ether moiety on the first vinyl ether unit of the polymer.
- the present invention provides novel poly(vinyl ether)
- A is a polyamine moiety having at least one basic
- R is a hydrocarbyl group having a sufficient -_ number of carbon atoms to render the poly(vinyl ether)
- R 2 is an alkylene group
- 21 are each independently hydrogen or a lower alkyl group
- H is an alkyl group
- n is an 4 integer from 5 to 99.
- the present invention further provides a fuel composition _ comprising a major amount of hydrocarbons boiling in the 8 gasoline or diesel range and an effective deposit- 9 controlling amount of a poly(vinyl ether) aminocarbamate of 0 the present invention.
- a fuel 3 concentrate comprising an inert stable oleophilic organic 4 solvent boiling in the range of from about 150°F to 400°F 5 and from about 10 to 70 weight percent of a poly(vinyl ether) aminocarbamate of the present invention.
- the present invention also provides a method for reducing engine deposits in an internal combustion engine comprising operating the engine with the aforementioned fuel composition containing an effective deposit-controlling amount of a poly(vinyl ether) aminocarbamate of the present invention.
- the present invention is based on the surprising discovery that fuel additives having a poly(vinyl ether) backbone have improved thermal stability and provide superior control of deposits, particularly on intake valves.
- the fuel additives provided by the present invention have the general formula:
- A is preferably a polyamine moiety derived from a polyamine containing 2 to about 12 amine nitrogen atoms and from 2 to about 40 carbon atoms. More preferably, A is a polyamine moiety derived from a polyalkylene polyamine containing 2 to about 12 nitrogen atoms and 2 to about 24 carbon atoms. Still more preferably, A is a polyamine moiety derived from a polyalkylene polyamine having the formula: H 2 N- (R 10 NH) y -H
- R 10 is alkylene having 2 to about 6 carbon atoms and y is an integer from 1 to 4.
- R is a hydrocarbyl group having at least 5 carbon atoms. More preferably, R, is a hydrocarbyl group having about 8 to about 120 carbon atoms. In a particularly preferred embodiment of the present invention, is alkyl having 8 to about 120 carbon atoms or alkylphenyl having an alkyl group containing 4 to about 100 carbon atoms. More preferably, R., is alkyl having 10 to 30 carbon atoms or alkylphenyl having an alkyl group containing 4 to 30 carbon atoms. Still more preferably, R 1 is alkylphenyl having an alkyl group containing 12 to 24 carbon atoms.
- R 2 is preferably alkylene having 2 to 4 carbon atoms. More preferably, R 2 is ethylene, i.e. -CH 2 CH 2 -.
- R 3 , R 4 , R 5 , R 6 , R 7 and Rg are each independently hydrogen, methyl or ethyl. More preferably, R 3 , R 4 , R g , R 6 , R 7 and R g are each independently hydrogen or methyl. Most preferably, R 3 , R 4 , R 5 , R 6 , R 7 and Rg are hydrogen.
- R 9 is preferably alkyl having 1 to 6 carbon atoms. More preferably, R, is alkyl having 2 to 4 carbon atoms.
- n is an integer from 10 to 50. More preferably, n is an integer from 15 to 30.
- a preferred group of poly(vinyl ether) aminocarbamates are those of formula I wherein A is derived from a polyalkylene polyamine containing 2 to about 12 nitrogen atoms and 2 to about .24 carbon atoms; R., is alkyl having 8 to about 120 carbon atoms or alkylphenyl having an alkyl group containing 1 4 to about 100 carbon atoms; R 2 is alkylene having 2 to 4 2 carbon atoms; R 3 , R 4 , R 5 , R 6 , R 7 and Rg are each independently 3 hydrogen, methyl or ethyl; R, is alkyl having 1 to 6 carbon 4 atoms; m is 0 or 1; and n is an integer from 10 to 50.
- a more preferred group of poly(vinyl ether) aminocarbamates 7 are those of formula I wherein A is derived from a 8 polyalkylene polyamine having the formula: 9 0 H 2 N-(R 10 NH) y -H 1 2 wherein R 10 is alkylene having 2 to about 6 carbon atoms and 3 y is an integer from 1 to 4; R, is alkyl having 10 to 30 4 carbon atoms or alkylphenyl having an alkyl group containing 5 10 to 30 carbon atoms; R 2 is ethylene; R 3 , R 4 , R g , R 6 , R 7 and 6 R g are each hydrogen; R, is alkyl having 2 to 4 carbon 7 atoms; m is 0 or 1; and n is an integer from 10 to 50. 8 9 A particularly preferred group of poly(vinyl ether) 0 aminocarbamates are those having the formula: 1
- the poly(vinyl ether) aminocarbamates of the present 2 invention will generally have a sufficient molecular weight 3 so as to be non-volatile at normal engine intake valve 4 operating temperatures. Typically, the molecular weight of 5 the poly(vinyl ether) aminocarbamates of this invention will range from about 600 to about 10,000, preferably from 1,000 to 3,000.
- hydrocarbyl refers to an organic radical primarily composed of carbon and hydrogen which may be aliphatic, alicyclic, aromatic or combinations thereof (e.g. aralkyl or alkaryl) .
- Such hydrocarbyl groups are generally relatively free of aliphatic unsaturation, i.e. olefinic or acetylenic unsaturation, but may contain minor amounts of heteroatoms, such as oxygen or nitrogen, or halogens, such as chlorine.
- alkyl refers to both straight- and branched-chain alkyl groups.
- lower alkyl refers to alkyl groups having 1 to about 6 carbon atoms and includes primary, secondary and tertiary alkyl groups. Typical lower alkyl groups include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl and the like.
- alkylene refers to straight- and branched-chain alkylene groups having at least 2 carbon atoms. Typical alkylene groups include, for example, ethylene (-CH 2 CH 2 -) , propylene (-CH 2 CH 2 CH 2 -) , isopropylene (-CH(CH 3 )CH 2 -) , n- butylene (-CH 2 CH 2 CH 2 CH 2 -) , sec-butylene (-CH(CH 2 CH 3 )CH 2 -) and the like.
- vinyl ether refers to an ⁇ ,3-unsaturated ether having the general formula:
- R a and R j are generally hydrogen or lower alkyl groups; and R c is a hydrocarbyl group.
- alkyl vinyl ether refers to a vinyl ether in which the hydrocarbyl group, R c , is an alkyl group.
- poly(vinyl ether) refers to a vinyl ether polymer having the general formula:
- vinyl ether unit refers to one monomeric unit of a poly(vinyl ether) polymer.
- z is an integer greater than 1.
- the poly(vinyl ether) aminocarbamates of this invention may be prepared by the following general methods and procedures. It should be appreciated that where typical or preferred process conditions (e.g. reaction temperatures, times, mole ratios of reactants, solvents, pressures, etc.) are given, other process conditions may also be used unless otherwise stated. Optimum reaction conditions may vary with the particular reactants or solvents used, but such conditions can be determined by one skilled in the art by routine optimization procedures.
- the poly(vinyl ether) aminocarbamates of the present invention contain (a) a poly(vinyl ether) component, (b) an amine component, and (c) a carbamate connecting group which covalently-links the poly(vinyl ether) component and the amine component.
- the poly(vinyl ether) component of the poly(vinyl ether) aminocarbamates of the present invention is a vinyl ether polymer containing about 6 to about 100 vinyl ether units, including a hydrocarbyl vinyl ether unit and about 5 to about 99 alkyl vinyl ether units.
- the poly(vinyl ether) component will have a hydrocarbyl vinyl ether unit at the beginning of the vinyl ether polymer and will be terminated with a branched or unbranched ethylene group containing 2 to about 10 carbon atoms which is covalently- linked to the carbamate connecting group.
- the poly(vinyl ether) component of the poly(vinyl ether) aminocarbamates of this invention is preferably prepared by polymerizing certain defined vinyl ether monomers under "living polymerization" conditions.
- the term "living polymerization” is well known in the art and refers to polymerization reactions which occur in the substantial absence of chain transfer and termination reactions. Under such conditions, the reactive end of the growing polymer is essentially stable indefinitely. Accordingly, each vinyl ether monomer can be added sequentially to the growing poly(vinyl ether) chain in a controlled step-by-step manner.
- living polymerization allows poly(vinyl ethers) to be prepared having a substantially predictable sequence of vinyl ether units.
- the living polymerization reaction is initiated using a hydrocarbyl vinyl ether monomer.
- Alkyl vinyl ether monomers are then added sequentially in an amount sufficient to produce the desired number of vinyl ether units.
- the reaction is then quenched under suitable aqueous conditions to form a carbonyl-terminated poly(vinyl ether) and the carbonyl group of the polymer is reduced to form a hydroxyl group.
- the resulting hydroxy-terminated poly(vinyl ether) is then coupled to a suitable amine component using phosgene or a phosgene equivalent to form the poly(vinyl ether) aminocarbamates of the present invention, as described in further detail below.
- the poly(vinyl ether) aminocarbamates of the present invention contain a hydrocarbyl ether moiety having a sufficient number of carbon atoms to render the poly(vinyl ether) aminocarbamate soluble in hydrocarbons boiling in the gasoline or diesel fuel range. This solubility condition is satisfied if the poly(vinyl ether) aminocarbamate is soluble in hydrocarbon fuel at least to the extent of about 50 parts per million by weight.
- the hydrocarbyl ether moiety will contain at least about 5 carbon atoms, preferably about 8 to about 120 carbon atoms, and more preferably 10 to 36 carbon atoms.
- the hydrocarbyl ether moiety of the poly(vinyl ether) aminocarbamates of this invention is generally introduced into the poly(vinyl ether) component by employing a hydrocarbyl vinyl ether monomer to initiate or begin the living polymerization reaction.
- Suitable hydrocarbyl vinyl ether monomers have the formula:
- R---R 4 and m are as defined above.
- hydrocarbyl vinyl ethers of formula III where m is 0 may be conveniently prepared from a monohydroxy compound and an olefin as represented by the reaction:
- R 1f R 3 and R 4 are as defined above.
- This reaction is catalyzed with a Group VIII noble metal compound, such as platinum and palladium chloride, and requires a regenerative oxidant capable of maintaining the noble metal in oxidized form, such as cupric chloride.
- a Group VIII noble metal compound such as platinum and palladium chloride
- a regenerative oxidant capable of maintaining the noble metal in oxidized form, such as cupric chloride.
- the reaction conditions are further described in U.S. Patent Nos. 4,057,575 and 4,161,610, both to D.L. Klass, the disclosures of which are incorporated herein by reference.
- hydrocarbyl vinyl ethers of formula III where m is 0 can be prepared by a vinyl exchange reaction.
- Vinyl ethers and esters readily exchange their vinyl groups with hydroxy compounds in presence of a catalyst, such as palladium or mercury salts, according to the reaction:
- hydrocarbyl vinyl ether monomers for use in the present invention are those of formula III where m is 1. These monomers can be conveniently prepared by reacting a monohydroxy compound, R-,0H or a suitable salt thereof, with a haloalkyl vinyl ether having the formula:
- R 2 , R 3 and R 4 are as defined above and Y is a halogen, such as chloride, bromide or iodide.
- R 3 and R 4 are hydrogen and R 2 is an alkylene group containing 2 to 4 carbon atoms.
- R 2 is ethylene (-CH 2 CH 2 -) and Y is chloride.
- the reaction of a monohydroxy compound, R.,0H or a suitable 5 salt thereof, with a haloalkyl vinyl ether of formula IV is 6 typically conducted by contacting the monohydroxy reactant 7 with about 1.0 to about 2.0 molar equivalents of the 8 haloalkyl vinyl ether in an inert solvent, such as 9 dimethylformamide (DMF) , dimethyl sulfoxide (DMSO) and the 0 like, at a temperature ranging from about 30°C to about 1 120 ⁇ C for about 1 to about 24 hours. Under these 2 conditions, the monohydroxy compound, R- ⁇ H, substantially 3 displaces the halogen forming the desired hydrocarbyl vinyl 4 ether monomers of formula III wherein m is 1.
- an inert solvent such as 9 dimethylformamide (DMF) , dimethyl sulfoxide (DMSO) and the 0 like
- the monohydroxy compound R ⁇ H, used in the above reactions, 6 is preferably a straight- or branched-chain aliphatic 7 alcohol having 8 to about 120 carbon atoms, more preferably 8 10 to 30 carbon atoms; or an alkylphenol having an alkyl 9 substituent containing about 4 to about 100 carbon atoms, 0 more preferably 10 to 30 carbon atoms, still more preferably 1 12 to 24 carbon atoms.
- 2 3 Preferred straight-chain alcohols have about 8 to about 30 * carbon atoms and include, for example, octanol, nonanol, 5 decanol, hexadecanol (cetyl alcohol) , octadecanol (stearyl alcohol) and the like.
- Particularly preferred straight- chain alcohols are those derived from linear C 10 to C 30 alpha olefins and mixtures thereof.
- Preferred branched-chain alcohols include those derived from polymers of C 2 to C 6 olefins, such as alcohols derived from polypropylene and polybutene. Particularly preferred are polypropylene alcohols having 9 to about 60 carbon atoms and polybutene alcohols having 8 to about 120 carbon atoms. Alcohols derived from the alpha olefin oligomers of C 8 to C 16 alpha olefins, such as the dimer, tri er and tetramer of decene as described in U.S. Patent No. 4.045,508, issued August 30, 1977 to B. L. Cupples et al., are also useful in this invention.
- the monohydroxy compound, R ⁇ H, used to prepare the hydrocarbyl vinyl ether monomers of formula III is an
- alkylphenol having the formula:
- R 14 is a straight- or branched-chain alkyl group having about 4 to about 100 carbon atoms, preferably 10 to 30 carbon atoms, more preferably 12 to 24 carbon atoms; and v is 1 or 2, preferably 1.
- the alkylphenol of formula V is a monoalkylphenol and when v is two, the alkylphenol is a dialkylphenol. Both mono- and dialkylphenols or mixtures thereof are suitable for use in the present invention, although monoalkylphenols are preferred. Most preferably, the alkylphenol of formula V is a monoalkylphenol having the alkyl group in the para position.
- the alkylphenols of formula V are prepared by reacting an olefin or olefin mixture with phenol in the presence of an alkylation catalyst.
- Suitable alkylation catalysts include sulfonic acid catalysts, such as Amberlyst® 15, and Lewis acid catalysts, such as boron trifluoride etherate.
- the alkylation reaction is typically conducted at a temperature from about 25°C to about 125°C.
- the reaction may be conducted in an essentially inert solvent or in the absence of a solvent. Examples of inert solvents include chlorobenzene and hexane.
- Monoalkylphenols may be preferentially prepared by employing an excess of phenol in the alkylation reaction, typically 2 to 2.5 equivalents of phenol for each equivalent of olefin. The excess phenol is preferably recovered and recycled.
- Dialkylphenols may be preferentially prepared by employing a molar excess of olefin in the alkylation reaction, such as two or more equivalents of olefin per equivalent of phenol.
- Preferred monoalkylphenols for use in the present invention include, for example, decylphenol, undecylphenol, dodecylphenol, tetradecylphenol, pentadecylphenol, hexadecylphenol, octadecylphenol, eicosylphenol, hexacosylphenol, triacontylphenol and the like.
- mixtures of alkylphenols may be employed, such as a mixture of C 14 -C 18 alkylphenols, a mixture of C 18 - 24 alkylphenols, a mixture of C 20 -C 24 alkylphenols, or a mixture of C 16 -C 26 aIkylpheno1s.
- alkylphenols are those derived from alkylation of phenol with polymers or oligomers of C 3 to C 6 olefins, such as polypropylene or polybutene. These polymers typically contain about 9 to about 100 carbon atoms, preferably about 10 to about 30 carbon atoms.
- An especially preferred alkylphenol is prepared by alkylating phenol with a propylene polymer having an average of 4 units. This polymer has the common name of propylene tetramer and is commercially available.
- Alkylphenols derived from alpha olefin oligomers of C 8 to C 16 alpha olefins, such as the dimer, trimer and tetramer of decene, are also useful in this invention. Such alkylphenols are described in PCT International Patent Application Publication No. WO 90/07564, published July 12, 1990, .the disclosure of which is incorporated herein by reference.
- the first vinyl ether unit of the poly(vinyl ether) component is typically derived from a hydrocarbyl vinyl ether monomer.
- the subsequent units of the polymer are preferably derived from alkyl vinyl ether monomers having the formula:
- R g , R 6 and R are as defined above.
- R g and R 6 are each independently hydrogen or methyl. More preferably, R g and R 6 are both hydrogen.
- the alkyl group ⁇ can be a straight- or branched-chain alkyl group and preferably contains 1 to 6 carbon atoms, more preferably 2 to 4 carbon atoms.
- Particularly preferred alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl and isobutyl groups.
- Especially preferred alkyl groups are ethyl and isobutyl groups.
- 07 aminocarbamates of this invention is preferably prepared by
- Lewis acid such as zinc iodide (Znl 2 ) or iodine (I 2 ) .
- 2i initiating systems may also be employed, such as a mixture
- the living polymerization reaction will be 9 conducted in a substantially anhydrous inert solvent at a 0 temperature of about -78 °C to about 50 °C, preferably -20 1 °C to 25 ⁇ C.
- Suitable inert solvents include benzene, 2 toluene, dichloromethane, diethyl ether and the like.
- the polymerization reaction will be conducted 4 5 under a dry inert gas atmosphere, such as nitrogen or argon, at about atmospheric or ambient pressure.
- a hydrocarbyl vinyl ether monomer of formula III is contacted with about 1.0 molar equivalents of hydrogen iodide to form an adduct according to the reaction:
- the hydrogen iodide is added as a solution in an inert solvent, such as hexane.
- This reaction is generally conducted for about 1.0 to about 20 minutes which is usually sufficient to result in the substantially complete conversion of the hydrocarbyl vinyl ether monomer to the adduct VII.
- an alkyl vinyl ether monomer of formula VI or a mixture of such alkyl vinyl ether monomers is added to the solution containing the adduct VII, and subsequently, zinc iodide is introduced to initiate the polymerization reaction.
- a molar ratio of hydrogen iodide to zinc iodide ranging from about 5:1 to about 500:1, preferably about 50:1, will be employed.
- the molar ratio of alkyl vinyl ether monomer to adduct VII will range from about 6:1 to about 100:1, preferably 11:1 to 51:1, more preferably 16:1 to 31:1.
- the alkyl vinyl ether monomer or mixture of monomers may be added entirely at the beginning of the polymerization reaction or may be added sequentially during the course of the reaction. By adding a mixture of alkyl vinyl ether monomers at the beginning of the reaction, a poly(vinyl ether) having an essentially random distribution of alkyl vinyl ether units can be produced. Alternatively, the sequential addition of different alkyl vinyl ether monomers produces a poly(vinyl ether) having substantial blocks of identical alkyl vinyl ether units.
- the time employed for the polymerization reaction can vary over a wide range and will depend to some extent on the reaction temperature and on the vinyl ether monomers used in the polymerization process. Generally, the reaction will be conducted for about 0.25 to about 20 hours, preferably 1.0 to 2.0 hours or until essentially all the alkyl vinyl ether monomers have reacted to form polymer. Completion of the polymerization reaction can be monitored by observing the disappearance of the vinylic proton(s) from the alkyl vinyl ether monomers by H NMR, if desired.
- the reactive terminal end of the polymer is quenched by contacting the reaction mixture with about 5 to about 20 equivalents of an aqueous alkali metal carbonate solution, such as aqueous potassium or sodium carbonate.
- an aqueous alkali metal carbonate solution such as aqueous potassium or sodium carbonate.
- -R f m and n are as defined above.
- the quenching reaction is typically conducted at about -20°C to about 25°C for about 0.1 to about 2 hours.
- the carbonyl group of the poly(vinyl ether) of formula VIII is reduced with a suitable reducing agent, such as a metal hydride reagent, to form a hydroxy-terminated poly(vinyl ether) having the formula:
- R---R , m and n are as defined above.
- a particularly preferred reducing agent is sodium borohydride.
- the reduction reaction is effected by contacting the carbonyl-terminated poly(vinyl ether) of formula VIII with about 2 to about 10 molar equivalents of sodium borohydride in an essentially inert solvent.
- suitable solvents include methanol, ethanol, propanol and the like. Ethanol is a particularly preferred solvent.
- the reaction is usually conducted at about 0°C to about 40°C for about 2 to about 24 hours.
- Other suitable methods for reducing carbonyl compounds to alcohols can be found, for example, in I.T. Harrison and S. Harrison, Compendium of Organic Synthetic Methods, pp. 81-84 and 111-118, Wiley- Interscience, New York (1971) and references cited therein.
- the hydroxy-terminated poly(vinyl ether) of formula IX may then be coupled with a suitable amine component using phosgene or a phosgene equivalent as described in further detail below.
- phosgene or a phosgene equivalent as described in further detail below.
- the poly(vinyl ether) aminocarbamates of the present invention contain an amine component which is covalently linked to the aforementioned poly(vinyl ether) component through a carbamate connecting group.
- the amine component will contain an average of at least about one basic nitrogen atom per molecule.
- a "basic nitrogen atom” is one that is titratable by a strong acid, for example, a primary, secondary or tertiary amine nitrogen; as distinguished from, for example, an carbamyl nitrogen, e.g. -OC(0)NH-, which is not titratable with a strong acid.
- at least one of the basic nitrogen atoms of the amine component will be primary or secondary amine nitrogen, more preferably at least one will be a primary amine nitrogen.
- the amine component of the poly(vinyl ether) aminocarbamates of this invention is preferably derived from a polyamine containing 2 to about 12 amine nitrogen atoms and from 2 to about 40 carbon atoms. Polyamines having a carbon-to-nitrogen ratio of from about 1:1 to 10:1 are particularly preferred.
- Suitable polyamines can have a straight- or branched-chain structure and may be cyclic or acyclic or combinations thereof. Generally, the amine nitrogen atoms of such polyamines will be separated from one another by at least two carbon atoms, i.e. polyamines having an aminal structure are not suitable.
- the polyamine may also contain one or more oxygen atoms, typically present as an ether or a hydroxyl group.
- polyamines for use in the present invention are polyalkylene polyamines, including alkylene diamines.
- Such polyalkylene polyamines will typically contain 2 to about 12 nitrogen atoms and 2 to about 24 carbon atoms.
- the alkylene groups of such polyalkylene polyamines will contain from 2 to about 6 carbon atoms, more preferably from 2 to 4 carbon atoms.
- suitable polyalkylene polyamines include ethylenediamine, propylenediamine, isopropylenediamine, butylenediamine, pentylenediamine, hexylenediamine, diethylenetriamine, dipropylenetriamine, diisopropylenetriamine, dibutylenetriamine, di-sec- butylenetriamine, triethylenetetraamine, tripropylenetetraamine, triisobutylenetetraamine, tetraethylenepentamine, pentaethylenehexamine and mixtures thereof.
- Particularly suitable polyalkylene polyamines are those having the formula:
- R 10 is a straight- or branched-chain alkylene group having 2 to about 6 carbon atoms, preferably 2 to 4 carbon atoms, most preferably 2 carbon atoms, i.e. ethylene (-CH 2 CH 2 -) ; and y is an integer from 1 to 4, preferably 1 or 2.
- Particularly preferred polyalkylene polyamines are ethylenediamine, diethylenetriamine, triethylenetetraamine and tetraethylenepenta ine. Most preferred is ethylenediamine.
- cyclic polyamines having one or more 5- to 6-membered rings.
- Such cyclic polyamines compounds include piperazine, 2-methylpiperazine, N-(2-aminoethyl)piperazine, N-(2-hydroxyethyl)piperazine, l,2-bis-(N-piperazinyl)ethane, 3-aminopyrrolidine, N-(2-aminoethyl)pyrrolidine and the like.
- the piperazines are preferred.
- polyamines suitable for use in present invention are commercially available and others many be prepared by methods which are well known in the art.
- methods for preparing amines and their reactions are detailed in Sidgewick's "The Organic Chemistry of Nitrogen", Clarendon Press, Oxford, 1966; Noller's “Chemistry of Organic Compounds”, Saunders, Philadelphia, 2nd Ed., 1957; and Kirk-Othmer•s "Encyclopedia of Chemical Technology", 2nd Ed., especially Volume 2, pp. 99-116.
- the carbamate connecting group which covalently links the poly(vinyl ether) component to the amine component has the formula:
- ether oxygen may be regarded as being derived from the hydroxyl group of a hydroxy-terminated poly(vinyl ether) of formula IX; and the nitrogen atom may be regarded as being derived from a nitrogen atom of a suitable amine component.
- the carbonyl group, -C(0)- is preferably provide by a carbonyl-containing coupling agent, such as phosgene or a phosgene equivalent. Economically, phosgene is the preferred coupling agent.
- suitable phosgene equivalents include, for example, 1,1'- carbonyldiimidazole, trichloromethyl chloroformate (diphosgene) and bis(trichloromethyl) carbonate (triphosgene) .
- the poly(vinyl ether) aminocarbamates of the present invention are preferably prepared by contacting a hydroxy- terminated poly(vinyl ether) of formula IX with phosgene to produce a poly(vinyl ether) chloroformate. The chloroformate is then contacted with a suitable polyamine to afford a poly(vinyl ether) aminocarbamate.
- the reaction of the hydroxy-terminated poly(vinyl ether) of formula IX with phosgene is typically conducted on an essentially equimolar basis, although excess phosgene can be used to increase the yield of the chloroformate. Excess phosgene is typically removed from the reaction mixture by stripping at reduced pressure before addition of the polyamine.
- the reaction may be conducted by contacting the hydroxy-terminated poly(vinyl ether) with phosgene at temperatures ranging from about -10°C to about 200°C, typically in an inert solvent, such as benzene, toluene and the like, for about 0.25 to about 5 hours.
- a poly(vinyl ether) aminocarbamate is then formed by contacting the poly(vinyl ether) chloroformate with a suitable polyamine at a temperature ranging from about 0°C to about 150°C for about 1 to about 24 hours.
- This reaction may be conducted with or without an inert solvent. Suitable inert solvents include benzene, toluene and the like.
- the molar ratio of polyamine to poly(vinyl ether) chloroformate will generally range from about 2:1 to about 20:1, preferably 5:1 to 10:1.
- the desired product may be obtained by washing the reaction mixture with water and stripping the mixture, usually under vacuum, to remove any residual solvent.
- the poly(vinyl ether) aminocarbamates of the present invention are useful as additives in hydrocarbon fuels to prevent and control engine deposits, particularly intake valve deposits.
- the desired deposit control will be achieved by operating an internal combustion engine with a fuel composition containing a poly(vinyl ether) aminocarbamate of the present invention.
- the proper concentration of additive necessary to achieve the desired deposit control varies depending upon the type of fuel employed, the type of engine, and the presence of other fuel additives.
- the concentration of the poly(vinyl ether) aminocarbamates of this invention in hydrocarbon fuel will range from about 50 to about 2500 parts per million (ppm) by weight, preferably from 75 to 1,000 ppm. When other deposit control additives are present, a lesser amount of the present additive may be used. Furthermore, lower concentrations of, for example, 30 to 70 ppm may be preferred when the present additives are employed as carburetor detergents only.
- the poly(vinyl ether) aminocarbamates of the present invention may be formulated as a concentrate using an inert stable oleophilic (i.e., dissolves in gasoline) organic solvent boiling in the range of about 150°F to 400°F (about 65°C to 205°C) .
- an aliphatic or an aromatic hydrocarbon solvent is used, such as benzene, toluene, xylene or higher-boiling aromatics or aromatic thinners.
- Aliphatic alcohols containing about 3 to 8 carbon atoms, such as isopropanol, isobutylcarbinol, n-butanol and the like, in combination with hydrocarbon solvents are also suitable for use with the present additives.
- the amount of the additive will be generally range from about 10 to about 70 weight percent, preferably 10 to 50 weight percent, more preferably from 10 to 25 weight percent.
- additives of the present invention including, for example, oxygenates, such as t-butyl methyl ether, antiknock agents, such as methylcyclopentadienyl manganese tricarbonyl, and other dispersants/detergents, such as hydrocarbyl amines, hydrocarbyl poly(oxyalkylene) amines, or succinimides. Additionally, antioxidants, metal deactivators and demulsifiers may be present.
- oxygenates such as t-butyl methyl ether
- antiknock agents such as methylcyclopentadienyl manganese tricarbonyl
- dispersants/detergents such as hydrocarbyl amines, hydrocarbyl poly(oxyalkylene) amines, or succinimides.
- antioxidants, metal deactivators and demulsifiers may be present.
- diesel fuels other well-known additives can be employed, such as pour point depressants, flow improvers, cetane improvers, and the like.
- a fuel-soluble, nonvolatile carrier fluid or oil may also be used with the poly(vinyl ether) aminocarbamates of this invention.
- the carrier fluid is a chemically inert hydrocarbon-soluble liquid vehicle which substantially increases the nonvolatile residue (NVR) , or solvent-free liquid fraction of the fuel additive composition while not overwhelmingly contributing to octane requirement increase.
- the carrier fluid may be a natural or synthetic oil, such as mineral oil, refined petroleum oils, synthetic polyalkanes and alkenes, including hydrogenated and unhydrogenated polyalphaolefins, and synthetic polyoxyalkylene-derived oils, such as those described, for example, in U.S. Patent No. 4,191,537 to Lewis.
- carrier fluids are believed to act as a carrier for the fuel additives of the present invention and to assist in removing and retarding deposits.
- the carrier fluid may also exhibit synergistic deposit control properties when used in combination with the poly(vinyl ether) aminocarbamates of this invention.
- the carrier fluids are typically employed in amounts ranging from about 100 to about 5000 ppm by weight of the hydrocarbon fuel, preferably from 400 to 3000 ppm of the fuel.
- the ratio of carrier fluid to deposit control additive will range from about 0.5:1 to about 10:1, more preferably from 2:1 to 5:1, most preferably about 4:1.
- carrier fluids When employed in a fuel concentrate, carrier fluids will generally be present in amounts ranging from about 20 to about 60 weight percent, preferably from 30 to 50 weight percent.
- reaction mixture 4 was stirred at -10 ⁇ C for 1.5 hours, then quenched with an
- the organic phase was washed three times with water, once with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered and the solvent removed in vacuo to give an oil.
- the oil was chromatographed on silica gel, eluting first with dichloromethane and then with dichloromethane/ isopropanol/ammonium hydroxide (9:0.9:0.1) to yield 6.0 grams of the desired product as a yellow oil.
- the product had an average of 22 ethoxyethylene units.
- thermogravimetric analysis TGA
- the TGA procedure employed a DuPont 951 TGA instrument coupled with a microcomputer for data analysis. Samples of the fuel additive (approximately 25 milligrams) were heated from 25°C to 700°c at 10°C per minute under air flowing at 100 cubic centimeters per minute. The temperature at which 95% weight loss occurred for each of the test samples was recorded and is shown in Table I. A higher 95% weight loss temperature indicates superior thermal stability.
- Comparative Example A 331°C 1 Comparative Example A was a dodecylphenyl poly(oxybutylene) ethylenediamine carbamate (having a molecular weight of about 1718) prepared in a manner similar to that described in Examples 6-8 of U.S. Patent No. 4,160,648 to Lewis et al.
- Example 6 The data in Table I demonstrates that a poly(vinyl ether) aminocarbamate of the present invention (Examples 4) has significantly increased thermal stability (>175 ⁇ C) compared to a known poly(oxyalkylene) aminocarbamate fuel additive.
- Example 6 The data in Table I demonstrates that a poly(vinyl ether) aminocarbamate of the present invention (Examples 4) has significantly increased thermal stability (>175 ⁇ C) compared to a known poly(oxyalkylene) aminocarbamate fuel additive.
- test compounds were blended in gasoline and their deposit reducing capacity determined in an ASTM/CFR single- cylinder engine test.
- a Waukesha CFR single-cylinder engine was used. Each run was carried out for 15 hours, at the end of which time the intake valve was removed, washed with hexane and weighed. The previously determined weight of the clean valve was subtracted from the weight of the value at the end of the run. The differences between the two weights is the weight of the deposit. A lesser amount of deposit indicates a superior additive.
- the operating conditions of the test were as follows: water jacket temperature 200°F; vacuum of 12 in Hg, air-fuel ratio of 12, ignition spark timing of 40° BTC; engine speed is 1800 rpm; the crankcase oil is a commercial 30W oil.
- the base fuel employed in the above single-cylinder engine tests was a regular octane unleaded gasoline containing no fuel detergent.
- the test compounds were admixed with the base fuel to give a concentration of 200 ppma (parts per million actives) .
- Table II illustrates the significant reduction in intake valve deposits provided by a poly(vinyl ether) aminocarbamate of the present invention (Examples 4) compared to the base fuel.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP94913955A EP0643760B1 (en) | 1993-04-01 | 1994-03-25 | Poly(vinyl ether) aminocarbamates and fuel compositions containing the same |
JP6522231A JPH07508292A (en) | 1993-04-01 | 1994-03-25 | Poly(vinyl ether) amino carbamate and fuel composition containing the same |
DE69413484T DE69413484T2 (en) | 1993-04-01 | 1994-03-25 | POLY (VINYL ETHER) AMINOCARBAMATE AND FUEL COMPOSITIONS CONTAINING THEM |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/041,734 US5306314A (en) | 1993-04-01 | 1993-04-01 | Poly(alkylene ether) aminocarbamates and fuel compositions containing the same |
US08/041,734 | 1993-04-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1994022986A1 true WO1994022986A1 (en) | 1994-10-13 |
Family
ID=21918047
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1994/003302 WO1994022986A1 (en) | 1993-04-01 | 1994-03-25 | Poly(vinyl ether) aminocarbamates and fuel compositions containing the same |
Country Status (6)
Country | Link |
---|---|
US (1) | US5306314A (en) |
EP (1) | EP0643760B1 (en) |
JP (1) | JPH07508292A (en) |
CA (1) | CA2136955A1 (en) |
DE (1) | DE69413484T2 (en) |
WO (1) | WO1994022986A1 (en) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08199179A (en) * | 1995-01-23 | 1996-08-06 | Nippon Oil Co Ltd | Additive to fuel oil and fuel oil composition containing the additive |
US5656040A (en) * | 1995-07-06 | 1997-08-12 | Chevron Chemical Company | Aminoaromatic ester polylactone aminocarbamates and fuel compositions containing the same |
CA2178663A1 (en) * | 1995-07-06 | 1997-01-07 | Richard E. Cherpeck | Polylactone aminocarbamates and fuel compositions containing the same |
CA2178662A1 (en) * | 1995-07-06 | 1997-01-07 | Chevron Chemical Company | Polyoxyalkylene polylactone aminocarbamates and fuel compositions containing the same |
US5618319A (en) * | 1996-06-20 | 1997-04-08 | Chevron Chemical Company | Alkylamine polylactone aminocarbamates and fuel compositions containing the same |
US5622532A (en) * | 1996-06-20 | 1997-04-22 | Chevron Chemical Company | Polylactone aromatic esters and fuel compositions containing the same |
EP0819753A1 (en) * | 1996-07-18 | 1998-01-21 | Nippon Oil Co. Ltd. | Fuel additive |
US6225415B1 (en) | 1999-09-20 | 2001-05-01 | University Of North Carolina At Charlotte | Process to selectively place functional groups within polymer chain |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4160648A (en) * | 1976-06-21 | 1979-07-10 | Chevron Research Company | Fuel compositions containing deposit control additives |
US4191537A (en) * | 1976-06-21 | 1980-03-04 | Chevron Research Company | Fuel compositions of poly(oxyalkylene) aminocarbamate |
US4197409A (en) * | 1978-08-08 | 1980-04-08 | Chevron Research Company | Poly(oxyalkylene)aminocarbomates of alkylene polyamine |
US4236020A (en) * | 1976-06-21 | 1980-11-25 | Chevron Research Company | Carbamate deposit control additives |
US4270930A (en) * | 1979-12-21 | 1981-06-02 | Chevron Research Company | Clean combustion chamber fuel composition |
US4274837A (en) * | 1978-08-08 | 1981-06-23 | Chevron Research Company | Deposit control additives and fuel compositions containing them |
US4288612A (en) * | 1976-06-21 | 1981-09-08 | Chevron Research Company | Deposit control additives |
US4778481A (en) * | 1983-08-08 | 1988-10-18 | Chevron Research Company | Diesel fuel and method for deposit control in compression ignition engines |
US4881945A (en) * | 1987-10-23 | 1989-11-21 | Chevron Research Company | Fuel compositions containing very long chain alkylphenyl poly(oxyalkylene) aminocarbonates |
US5192335A (en) * | 1992-03-20 | 1993-03-09 | Chevron Research And Technology Company | Fuel additive compositions containing poly(oxyalkylene) amines and polyalkyl hydroxyaromatics |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR8807893A (en) * | 1988-12-30 | 1990-12-11 | Chevron Res & Tech | LIQUID, COMPOUND, COMPOSITION AND CONCENTRATE POLY (OXYPROPYLENE) LIQUID, COMPOUND, COMPOSITION AND LUBRICANT OIL CONCENTRATE, AND ALKYLPHENOL |
-
1993
- 1993-04-01 US US08/041,734 patent/US5306314A/en not_active Expired - Fee Related
-
1994
- 1994-03-25 WO PCT/US1994/003302 patent/WO1994022986A1/en active IP Right Grant
- 1994-03-25 EP EP94913955A patent/EP0643760B1/en not_active Expired - Lifetime
- 1994-03-25 DE DE69413484T patent/DE69413484T2/en not_active Expired - Fee Related
- 1994-03-25 JP JP6522231A patent/JPH07508292A/en not_active Ceased
- 1994-03-25 CA CA002136955A patent/CA2136955A1/en not_active Abandoned
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4160648A (en) * | 1976-06-21 | 1979-07-10 | Chevron Research Company | Fuel compositions containing deposit control additives |
US4191537A (en) * | 1976-06-21 | 1980-03-04 | Chevron Research Company | Fuel compositions of poly(oxyalkylene) aminocarbamate |
US4236020A (en) * | 1976-06-21 | 1980-11-25 | Chevron Research Company | Carbamate deposit control additives |
US4288612A (en) * | 1976-06-21 | 1981-09-08 | Chevron Research Company | Deposit control additives |
US4197409A (en) * | 1978-08-08 | 1980-04-08 | Chevron Research Company | Poly(oxyalkylene)aminocarbomates of alkylene polyamine |
US4274837A (en) * | 1978-08-08 | 1981-06-23 | Chevron Research Company | Deposit control additives and fuel compositions containing them |
US4270930A (en) * | 1979-12-21 | 1981-06-02 | Chevron Research Company | Clean combustion chamber fuel composition |
US4778481A (en) * | 1983-08-08 | 1988-10-18 | Chevron Research Company | Diesel fuel and method for deposit control in compression ignition engines |
US4881945A (en) * | 1987-10-23 | 1989-11-21 | Chevron Research Company | Fuel compositions containing very long chain alkylphenyl poly(oxyalkylene) aminocarbonates |
US5192335A (en) * | 1992-03-20 | 1993-03-09 | Chevron Research And Technology Company | Fuel additive compositions containing poly(oxyalkylene) amines and polyalkyl hydroxyaromatics |
Also Published As
Publication number | Publication date |
---|---|
EP0643760B1 (en) | 1998-09-23 |
EP0643760A4 (en) | 1995-09-13 |
DE69413484D1 (en) | 1998-10-29 |
EP0643760A1 (en) | 1995-03-22 |
JPH07508292A (en) | 1995-09-14 |
US5306314A (en) | 1994-04-26 |
CA2136955A1 (en) | 1994-10-13 |
DE69413484T2 (en) | 1999-08-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5669939A (en) | Polyalkylphenoxyaminoalkanes and fuel compositions containing the same | |
US5752991A (en) | Very long chain alkylphenyl polyoxyalkylene amines and fuel compositions containing the same | |
EP0643760B1 (en) | Poly(vinyl ether) aminocarbamates and fuel compositions containing the same | |
WO1995011954A1 (en) | Fuel compositions containing poly(oxyalkylene) aromatic ethers | |
JPH08245536A (en) | Aromatic amide | |
EP0643758B1 (en) | Poly(vinyl ether) amines and fuel compositions containing the same | |
EP0832960B1 (en) | Aminocarbamates of polyalkylphenoxyalkanols and fuel compositions containing the same | |
CA2255519A1 (en) | Fuel compositions containing polyamines of polyalkyl aromatic esters | |
CA2226672C (en) | Fuel additive compositions containing polyalkyphenoxyaminoalkanes and poly(oxyalkylene) amines | |
EP0643759B1 (en) | Poly(alkylene ether) hydroxy (oxypropylene) amines and fuel compositions containing the same | |
EP0752439B1 (en) | Polylactone aminocarbamates and fuel compositions containing the same | |
EP0752438B1 (en) | Polyalkylene polylactone aminocarbamates and fuel compositions containing the same | |
EP0781794B1 (en) | Very long chain alkylphenyl polyoxyalkylene amines and fuel compositions containing the same | |
EP0926223A2 (en) | Fuel compositions containing polyamines of poly (oxyalkylene) aromatic esters |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): CA JP |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2136955 Country of ref document: CA |
|
CFP | Corrected version of a pamphlet front page | ||
CR1 | Correction of entry in section i | ||
WWE | Wipo information: entry into national phase |
Ref document number: 1994913955 Country of ref document: EP |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWP | Wipo information: published in national office |
Ref document number: 1994913955 Country of ref document: EP |
|
WWG | Wipo information: grant in national office |
Ref document number: 1994913955 Country of ref document: EP |